Azo-dyestuff



Patented Jan. 14, 1936 UNITED Aer FWC

AZO-DYESTUFF Gerald Bonhote, Basel,

Switzerland, assignor to the firm Society of Chemical Industry in Basle,

Basel, Switzerland No Drawing. Application May 9, 1935, Serial No. 20,679. In Switzerland May 19, 1934 6 Claims.

wherein R1 stands for an aryl radical of the benzene series and R2 for an alkyl radical, with an arylide of 2,3-hyolroxynaphthoic acid.

The new dyestufis correspond therefore to the general formula C-Rs CNRz t i in which R1 and R2 have the signification indicated above, and R3 represents an aromatic nucleus of the benzene or naphthalene series. They form red powders insoluble in water, dissolvingin organic solvents, such as pyridine, to red-orange solutions, and when produced on the fiber dye the same vivid scarlet to blue-red tints which are characterized by excellent fastness properties to light and bleaching. As for the fiber on which the new dyestuffs can be produced, there may be named cotton above all. The dyestuffs can however also be produced on regenerated cellulose, such as viscose artificial silk, on cellulose esters, such as acetate artificial silk, on natural silk or on wool. Further, they may also find application as pigments, for example for dyeing lacquers or varnishes.

Among these dyestuffs those are particularly valuable in which the radical R1 may stand for an aryl nucleus of the benzene series capable of being substituted, the radical R2 for an alkyl radical consisting of not too great a number of carbon atoms, for example one or two carbon (Cl. 26ll95) atoms, and the radical R3 for an aromatic nucleus of the benzene series. Among these dyestuffs those are again particularly valuable in which the benzene nucleus R3 contains at least one alkoxy-group, i. e. dyestuffs of the general formula in which R1 and R2 have the meaning indicated above and in which R3 stands for an aryl radical of the benzene series substituted in orthoor para-position to the liq-group H by an alkoxy-group.

The ketones of the general formula necessary for producing the new dyestuffs can be obtained quite generally by condensing with bromobenzene, carboxylic acid chlorides, such as acetyl chloride, propionyl chloride, butyryl chloride and the like, nitrating the ketone thus formed in ortho-position to the bromine atom, causing the bromine atom to react with a phenol, such as phenol, para-cresol, ortho-cresol, metacresol, para-chlorophenol and the like, and reducing the nitrated ethers thus obtainable.

The following examples illustrate the invention, the parts being by weight:

Example 1 22.7 parts of 2amino-4-acetyl-1,1'-diphenylether are diazotized in the usual manner. The clear diazo-soluti-on is introduced into a solution consisting of 31.1 parts of 2,3-hydroxynaphthoic acid-5'-chloro-2-methy1anilide, parts of sodiurn hydroxide solution of 30 per cent. strength,

15 parts of sodium carbonate and 2000 parts of water. The dyestuif thus formed of the formula I? 6 C CHI I OH C1 is immediately precipitated. The red precipitate is filtered and dried. The procedure is similar for example with the 2-amino-4-propionyl-1, 1- diphenylether or with the 2,3-hydroxynaphthoic acid-2', 4-dimethoxyor 2, i-diethoxyanilide.

Example 2 Cotton yarn is impregnated with a grounding made by dissolving '7 grams of 2,3-hydroxynaphthoic acid -2'-methylanilide in 300 cc. of hot water with addition of 12 cc. of caustic soda solution of per cent. strength and 10 cc. of Turkey red oil and diluting the whole to 1 litre. The goods are then wrung out and developed in a diazo-solution, buffered with sodium acetate and containing per litre the diazo-compound corresponding with 2 grams of 2-amino-4-acetyli-.

ch10ro-1,1'-diphenylether. There is produced a pure red of excellent properties of fastness. The formula of the new dyestuff is Similar red tints are obtained when there is used 2,5-dimethoxy-ani1ide, ZA-dimethoxy-S- chloranilide, 2-methyl-4-methoXy-anilide, 3,4-dichloranilide, 5-ch1oro-2-methyl-anilide, or 4- chloro-Z-methoxyanilide of 2,3-hydroxynaphthoic acid.

Scarlet red tints are obtained with the metatoluidide, meta-chloranilide, ortho-phenetidide, ortho-toluidide, 2- methoxy -5- methylanilide,

para-chloranilide, [3-naphthalide, ortho-anisidide,

para-toluidide or para-phenetidide of 2,3-hydroxynaphthoic acid.

Example 3 Cotton yarn is impregnated with a solution containing per litre 5.5 grams of 2,3-hydroxynaphthoic acid-4-methoxyanilide, 12 cc. of sodium hydroxide solution of 30 per cent. strength, 10 cc. of Turkey red oil, 6 cc. of formaldehyde solution of 40 per cent. strength, then well wrung out and developed in a diazo-sclution buffered with sodium acetate and containing per litre, the diazo-compound from 2 grams of Z-aminoiacetyli'-methyl-1,1'-diphenylether; rinsing and soaping follow. There is obtained a very pure red tint of very good properties of fastness. The

formula of the new dyestuff is (I) JlL-CHI E-I-OO CH:

rit H in which R1 stands for an aryl radical of the henzene series, R2 for an alkyl radical consisting of not more than two carbon atoms, and. R for a radical of the benzene or naphthalene series,

which dyestufis are red powders insoluble in water, but dissolving in pyridine to red-orange solutions, and which dyestuffs when prepared on the fiber, dye the same fast vivid scarlet to red tints.

2. The dyestuffs of the general formula 0 Rr-O in which R1 stands for an aryl radical of the benzene series, R2 for an alkyl radical consisting of F not more than two carbon atoms, and in which R3 stands for an aryl nucleus of the benzene series substituted in orthoor para-position to the NH- group by an alkoxy-group, which products are red powders insoluble in water, but dissolving in pyridine to red-orange solutions, and which dyestufis when prepared on the fiber, dye the same test vivid scarlet to red tints.

3. The dyestuffs of the general formula (i-CHn Rr-O- N II N I; CHv-O-O-Q which dyestufi is a red powder insoluble in water, but dissolving in pyridine to a red-orange solution, and which dyestufi, when produced on cotton, dyes this fiber fast red tints.

5. The dyestufi of the formula which dyestuff is a red powder insoluble in water, but dissolving in pyridine to a red-orange solution, and which dyestufi, when produced on cotton, dyes this fiber fast red tints.

6. The dyestuff of the formula OH OOH:

which dyestufi is a red powder insoluble in water, but dissolving in pyridine to a red-orange solution, and which dyestufi, when produced on cotton, dyes this fiber fast red tints.

GERALD BoNHo'I'E. 

